Lo & Sons — The Brookline

If you live in a rainy city, make the Brookline tote ($198, fits up to 15-inch laptops) your top pick. With its simple, sophisticated profile and an abundance of interior compartments, the Brookline is basically a working girl's dream. We've been reviewing the bag by Lo and Sons for a few months now, and it's kept our devices safe through the Winter months thanks to a hefty water-resistant nylon exterior.

Lo and Sons is known for making its gear travel-friendly with a signature back-panel sleeve that can slip over luggage handles. It's a great personal item to take with you on the plane, because the bag has a compact shape but can hold a ton of items. Just watch this video for proof. In fact, the Brookline can hold so much that I often overpacked, making the bag too heavy to carry on my shoulder.

The only downside? Too many pockets. We'd never thought we'd say such a thing, but many a time we were left fuddling with our bags for minutes, looking through all its pouches and sleeves for little trinkets.